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20 Lessons I Wish I Learned in my 20s

Hey everyone, and welcome to Episode 24 of The Darn Good Life Podcast. I’m your host, Danielle Roberts, and this month, I celebrated by 32nd birthday. So I thought I’d dedicate today’s episode to lessons I wish I had learned in my 20s. If you’ve listened to my show, you know that I am absolutely obsessed with personal and professional transformation, and the relentless pursuit of building a life that I love. So if you’re unhappy with where you are and feel stuck, yet ready for a breakthrough…this episode is for you.

Hello you beautiful humans. Thanks for being here with me today. I am going to jump right into the good stuff and give you 20 lessons that I wish I knew in my 20s…if any of these resonate with you, hit me up on Instagram at darnroberts. Would love to hear your thoughts and any lessons you’ve learned as you’ve gotten older. Ok great let’s get started…

Your degree is not as important as what lights your soul on fire and gets you excited.

Most people go to college because that’s what we’re supposed to do, right? Our parents told us that was the right thing to do…so we listened. And then a lot of us continued our education because the economy wasn’t great. The truth is, most of us pick something at random to pursue simply because we think we have to…but we haven’t had the real opportunity to even get to know ourselves yet. Science shows that our brains aren’t even fully developed until we’re around 26 years old.

I loved math in high school – I took AP calculus my senior year, so I went into college as a math major and thought I could make a decent living as an actuary. An actuary is someone who uses math and statistics to estimate the financial impact of uncertainty and help clients minimize risk. So if you’ve ever seen Along Came Polly, Ben Stiller was an actuary. 

So if you know me, that’s basically fucking hysterical. I don’t see things in numbers or in black and white. I feel things. So after my freshman year, I changed majors to psychology. After that, I dropped down to part-time for a semester because I was struggling…and then I changed to public relations and added advertising, which is what I eventually graduated with degrees in and the career path I pursued.

And since then, I have learned so much about what I don’t want in a career. In my 20s, I wish someone had told me that your bachelors or masters or certificate or whatever does not dictate what you will or will not do for the rest of your life. You don’t have to stay in the same job for 20, 30, 40 years like your parents have. You are allowed to change your mind, follow your gut, and pursue what excites you. There are a million ways to make a living, so remember at any time, you can pivot and follow what feels good.

Most people don’t ask the right questions. 

I had a revelation in my late 20s, into my early 30s after years of therapy and working 1:1 with coaches…and that’s that we ask ourselves really shitty questions that keep in a perpetual mindset of lack and negativity. These questions keep us feeling stuck.

Instead, we should reframe what we ask ourselves to truly better understand who we are deep down, separate from outside influence. So ask yourself…

  • What’s wrong with me versus what happened to me?
  • Is this happening to me or is this happening for me?
  • What do I need to do versus who do I need to become?

Reframing questions opens the right doors. Trust me on this one.

We are not our thoughts.

Have you ever heard the phrase that humans are basically cucumbers with anxiety? Most people live their entire lives in their mind – depression keeps them stuck in the past, and anxiety keeps them worried about the future. 

One of the biggest thing I’ve learned is that mindset is literally everything. We’re the only species that can observe our own thoughts.

We can be conscious enough to take ourselves away from the thought that we’re having and notice we’re having it. And once we do that, we can realize that our thoughts – or the story we tell ourselves – aren’t true. 

In other words, the mind adds its own narrative to everyday events which we accept as truth. This narrative is often negative. When we bring awareness to these thoughts as they happen rather than becoming invested in them, we can change that narrative.

This is something that takes real work…daily work…but is literally the key to unlocking mental liberation.

Action precedes motivation. 

I am a big fan of the phrase: If you wait until you’re ready, you’ll be waiting for the rest of your life. 

If you’re waiting until something is perfect, you’ll be waiting for the rest of your life. Perfectionism is really just fear wearing a mask. Motivation is just a feeling. The only thing we need to do to get the life we want is to take action. The results we get from taking action – taking relentless, CONSISTENT action – reinforce new outcomes that leave us then feeling more motivated, more confident, and more capable.

Be selfish.

Or, as I prefer to say, stop making yourself available for anything that makes you feel like shit. People aren’t entitled to you, your time, or your energy, and you need to protect your boundaries at all costs. 

Just because people are family, or just because you’ve been friends with someone for however long, does not mean they are entitled to any part of you.

You’re not responsible for other people’s bullshit. You’re out here working on you, and that threatens and intimidates people who aren’t willing to confront the ugly parts of themselves.

Do yourselves a favor, and remove those people from your life – and if you can’t fully remove them, limit your exposure to them.

Do not ever take advice from someone who isn’t living the life you want to live. Be selfish in pursuit of building the life you want. You’re going to outgrow people and shed layers off the old you along the way…and that’s okay.

Learn more about how money works and how to invest. 

And know the difference between assets and liabilities. In its simplest terms, assets are the items you own that can provide future economic benefit. Liabilities are what you owe other parties. For example, an asset would be a property you rent out to tenants, and a liability would be a car payment.

I learned only a couple years ago that the average millionaire has 7 streams of income. And if you continue to trade time for dollars, keep your savings in a low-interest savings account, and never learn to make your money work for you, you won’t be able to accumulate wealth (unless, of course, you are born into generational wealth or somehow come into a significant sum of money).

This is 1000% something I wish I knew sooner. Start off and download the app Mint (it’s free) to see where your money is going and how much you can divert into something that will make you more money. You will be AMAZED how much you spend on shit you don’t need. And it’s no wonder we didn’t get taught this in school…because we live in a capitalistic society designed to keep us stuck in the socioeconomic state we’re in, in order to put more dollars in the hands of the wealthy (and yes, this includes politicians, banks, and big pharma, who all don’t give a damn about any of us). Take that power back and take control of your finances by creating monthly budgets and sticking to them.

And if you don’t have the time, hire someone. Just start somewhere. Aim to hire an independent advisor who’s a true fiduciary, who believes in selecting a well diversified portfolio of index funds. But on the flip side…my next lesson…

Money doesn’t matter. 

My dad always says that you don’t see the armored car behind the hearse. 

Our society ranks how much people are worth by the amount of money they make. At one point, we’ve all aspired to have those big houses and fancy cars. 

So, after we graduated with that degree we may or may not have wanted or needed…we take our next step, leading with how much money we want to make. I recorded an entire episode about money, so go check out Episode 3 if you haven’t already…but while money is of course important to our survival, it should not be everything to us.

Instead, we should lead with our “why.” Why do we want to do what we want to do?

Listen…at your funeral when your loved ones are eulogizing you, no one is going to make a speech about how much money you had or what kind of car you drove. They’re going to talk about your character and the mark you made during your short stay here on earth.

Love is a verb. 

Romantic, familial, friendship, or otherwise…the best relationships thrive because people actively participate in that relationship.I spent a lot of my time with people who didn’t deserve my attention, trying to prove my worth.

Love means constantly putting in the work; showing up when your people need you the most; it’s about accepting them and loving them for exactly who they are, and supporting them through the process.

Everyone gives and receives love differently. The biggest action you can take in any relationship is learning how to communicate. Learning how to be a better communicator will improve your relationships tenfold. Because you’ll be able to state your needs in a healthy manner and recognize when triggers come up for the people that you love, which in turn will help you help them through it, thereby making your relationships stronger.

And this is especially true when it means loving ourselves…which leads me to my next lesson…

Stop with the negative self talk. 

In my 20s, I came across a quote that gave me pause, and it goes: “And if I asked you to name all the things that you love, how long would it take for you to name yourself?”

We need to learn to love ourselves. It’s so cliche, but it’s true. I really wish I would’ve known to appreciate and honor my body more in my 20s. I remember comparing myself to so many people, especially in college. Thinking I wasn’t pretty enough, or skinny enough, or smart enough. And even today, I’ll look back at photos and say “damn I wish I was still that skinny!”

We would never, ever, EVER talk to our friends the way we talk to ourselves. So why do we think it’s ok to talk to ourselves like a piece of trash?

You are the only you that will ever exist. You have a lot to offer this world, and you are enough. 

The importance of goal setting.

A Harvard Business Study found that the 3% of graduates from their MBA who had their goals written down, ended up earning ten times as much as the other 97% put together, just ten years after graduation.

Goal setting is a science. If we have arbitrary goals like like weight or find a job I love, we aren’t setting ourselves up for success. We need to create a plan, break it down into bite-sized chunks, and consistently check in to ensure we’re making progress. Set SMART goals – SMART is an acronym for specific, measurable, actionable, realistic, and time-bound.

And the truth is, sometimes reaching that goal looks very different than what you originally intended, but it’s about who you become in that process of pursing the goal. It’s all about the vision.

People you love won’t be here forever.

You’ve heard me talk plenty about losing my mom when I was 23. I skipped so many of her phone calls and so many family dinners because I was hustling to climb the corporate ladder, pulling late nights at the office, then going out and partying. Looking back, I wish I answered more of those calls, or paid more visits to her on the weekend.

Losing someone you love is earth-shattering; there’s no way around that. Nothing can prepare you for it, and you don’t understand it until you go through it. So take it from me and go call your loved ones and tell them you love them; make time to see them even if it’s just over Facetime or an “I’m thinking of you” text. It takes two seconds, and we can all make the time.

You don’t have to follow society’s path to be successful. 

What even is success, anyway? Working until you retire so you can enjoy life when you’re old? HELL NO. If you’d rather go to trade school than college, do it. If you want to be an artist, create. If you hate your job, find another one. The direction you’re going is more important than the speed at which you’re traveling.

Wherever you are right now, in this very moment, is exactly where you were meant to be. Be patient, continue showing up for yourself with intention, and you’ll arrive where you’re meant to go.

Success is an arbitrary term. Figure out what living a successful, happy life means to YOU and pursue what will get you closer to that feeling.

You’re not stuck. 

You are not a tree. Uproot and move if you don’t like your environment. This could mean where you live. This could mean your shitty job. This could mean your relationships. This could even mean your unhealthy habits.

At any point, we have the option to choose. We can choose to leave our current situations. Leaving our current situation for the freedom or love or peace we desire requires us to leave what’s comfortable and familiar.

One of my favorite sayings ever – and I learned this from one of my coaches – is to choose your hard. 

Staying in a job you hate is hard, so is applying elsewhere or building a business. Choose your hard.

Eating like shit and sitting all the time is hard. Fueling your body with good food and moving daily is hard. Choose your hard.

Breaking up with someone or getting divorced is hard. Staying in a toxic relationship is hard. Working to be a better communicator and understanding how to love better to repair your relationship is hard. Choose your hard.

Most things in this life are flexible and fluid. We know only one thing for certain: we’re all going to die. So don’t waste whatever time you have left choosing to do shit you don’t want to do.

Investing in yourself pays off. 

You are the greatest asset you will ever have. And I don’t mean self-care days.

I mean the stuff that will aid in your personal transformation. The absolute best thing I ever did for myself was get mentors and hire a coach, go to therapy for five years, and surround myself with communities that elevated my mentality, and made me demand more from myself. Have you ever heard the saying, “If you’re the smartest person in the room, you’re in the wrong room”? 

Approach every person you meet as if there is something new you can learn from them.

Sometimes it takes spending a few dollars to save yourself a ton of time, and learn from people who have done it before. For you, that could be hiring a coach, listening to podcasts, buying books, or taking classes…but treat yourself to what will undoubtedly help you accelerate the timeline toward who you want to become.

You can do anything but not everything.

I continue to get myself into trouble with this one. I am multi-passionate and believe life is too short to be just one thing. But when we become laser-focused on making progress in only ONE area, progress happens much quicker. Seriously, if you focus on ONE thing only for the next 6 months, you could have a completely different life.

In Shea and my business, Tail of Two Creatives, we started by offering all these digital marketing services and quickly scaled back to stay hyper-focused on building websites. We wanted to be able to give 100% of ourselves to one thing rather than 10% of ourselves to 10 different things.

I’m guilty of having shiny object syndrome – bouncing around to things. If you don’t have a strong enough “why” attached to what you’re doing, it’ll be hard to stay focused. So make sure you spend time journaling out what’s actually important to you.

And remember, you still have worth even when you aren’t being hyper-productive every single hour of every day. Actively resting also counts as doing something.

Give back.

Give back especially to those less fortunate. Find a way to pay it forward. Not everyone is afforded the circumstances we are. Whether it’s lending an ear, lending a hand, or lending a dollar, find causes you care about and do what you can. 

Just find a way to get involved in something you care about because it really makes a difference, and you’ll find joy in leaving this world better than you found it.

And here, I would challenge you to give back to the Earth. There’s a lot we do to abuse the very place that we live, and it has serious consequences. Consider what you can do to make less of an environmental impact to ensure this planet has longevity for every species. 

Find your tribe.

And focus on quality over quantity. It’s important to surround yourself with people who are loving, kind, and supportive of your goals. Who you spend the most time with is who you eventually become. So if you surround yourself with people who love to drink all the time, you’re more likely to drink. But if you surround yourself with successful business owners, you’re likely to become the next one. 

According to research by social psychologist Dr. David McClelland of Harvard, [the people you habitually associate with] determine as much as 95 percent of your success or failure in life.

Your goals may be bigger than the environment in which you find yourself. Sometimes you have to get out of that environment and expose yourself to new tribes to actualize those goals. Take time to find those people who elevate you and give you energy rather than the opposite.

Put your damn phone down.

The average person spends at least almost 2 ½ hours on social media per day. That’s an extra 16 hours per week you can find to do the things you say you want to do. You DO have the time, you’re just wasting over a month of your time every year scrolling through Instagram.

Do you want to wake up one day and realize you lived your entire life watching other people live the life you want to live through your phone? You don’t squeeze the juice out of life by staring at a screen, constantly consuming other people’s highlight reels or digesting around-the-clock news that’s perpetually negative. 

Put your phone down, start having deep conversations with people in the same room as you, go take a walk in nature, make a friend. Be present in the moments you’re in.

Dogs make everything better!

This one is short and sweet for obvious reasons…I don’t ever want to live in a world without dogs, and adopting ours was the best thing I ever did.

Last but not least…Enjoy the journey.

There’s never going to be a day when you arrive at happy. Like the literal point of being alive is to enjoy the journey, the process of becoming who were meant to be, the thrill of experiencing breathing and enjoying the tastes, sights, smells, touches, and sounds of being on a planet that’s traveling and solar speeds, just spinnin’ through the universe. Like how fucking cool is that? 

I spent so much time in my 20s looking for my quote-unquote purpose – that I didn’t even realize that I was walking in it.

I came across a piece of content from creator Jasmines Garden on Tiktok, and she said: 

“Why do we limit our purpose to one major moment or contribution in life when we have so many moments where we contribute purposeful things, even if it’s not for us but for someone else? Why do we feel our purpose doesn’t grow and change day to day as we do? Maybe we should stop telling people to find their purpose, and just start teaching them to be intentional? Maybe your purpose today is to help a friend laugh as they’re fighting to focus through their tears. And maybe tomorrow, it’s for you to try a new recipe or new restaurant, just for the purpose of experience. Maybe our purpose in life is just to start doing things on purpose instead of out of programming.”

And with THAT MIC DROP, my friends, I’m gonna leave you the same way I do every episode…LIfe is short, so go make it a darn good one. Please share this with someone you love if you’ve been listening and getting value out of my show…my goal is to connect and help as many people as I possibly can. I appreciate you listening, and I hope you have an incredible day.

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Hey, I'm Danielle!

I’m a multi-passionate, queer entrepreneur, coach, and podcast host obsessed with personal development and the relentless pursuit of building a life that I love.

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